Biosynthesis of unnatural morphine derivatives in Papaver somniferum

Abstract

Demethylation of various codeine derivatives to give the corresponding, unnatural derivatives of morphine has been studied in Papaver somniferum. The efficiencies of the unnatural processes have been compared with that of the natural, codeine into morphine, conversion by feeding mixtures of [2-³H]-labelled codeine derivatives with [N-methyl-¹⁴C]codeine. Demethylation of dihydrocodeine (efficiency relative to codeine into morphine conversion, 47%), isocodeine (15%), codeine methyl ether (69%), dihydrodeoxycodeine (108%), and 1-bromocodeine (5.8%), to give the corresponding morphines, was observed.